4-OH-IndAcOrnAsn5ßAla4ßAla4ßAla4
General Description
| Name | Value |
|---|---|
| Level | S-4 / C-3 |
| Discovered | 1996 / N. clavata |
| Synonym | Nephilatoxin 4 / NPTX 4 |
| Molecular formula | C₄₅H₇₉N₁₃O₈ |
| CAS | — |
| SMILES | O=C(CC1=CNC2=C1C(O)=CC=C2)NC(C(CCCN)NC(CC(N)=O)C(NCCCCCNC(CCNCCCCNC(CCNCCCCNC(CCNCCCCN)=O)=O)=O)=O)=O |
| InChI | InChI=1S/C45H79N13O8/c46-18-2-5-20-49-27-15-40(62)53-24-8-7-22-51-29-17-41(63)54-25-9-6-21-50-28-16-39(61)52-23-3-1-4-26-55-44(65)36(31-38(48)60)57-35(13-11-19-47)45(66)58-42(64)30-33-32-56-34-12-10-14-37(59)43(33)34/h10,12,14,32,35-36,49-51,56-57,59H,1-9,11,13,15-31,46-47H2,(H2,48,60)(H,52,61)(H,53,62)(H,54,63)(H,55,65)(H,58,64,66) |
| Precursor 1 [M+H]⁺ | 930.62473 |
| Precursor 2 [M+2H]²⁺ | 465.81600 |
| Precursor 3 | |
| HDX | 17 |
| Precursor HDX 1 [M(D₁₇)+D]⁺ | 948.73771 |
| Precursor HDX 2 [M(D₁₇)+2D]²⁺ | 475.37563 |
| Precursor HDX 3 | |
| Rt | |
| Rt HDX |
Calculated MS/MS fragments
| # | a | b | c | ta | z | y | tz |
|---|---|---|---|---|---|---|---|
| 1 | 288.13427 | 270.12370 | 271.10772 | 305.16082 | 72.08078 | 55.05423 | 89.10732 |
| 2 | 402.17720 | 384.16663 | 385.15065 | 419.20374 | 143.11789 | 126.09134 | 160.14444 |
| 3 | 487.26634 | 469.25578 | 470.23980 | 504.29289 | 214.19139 | 197.16484 | 231.21794 |
| 4 | 558.30346 | 540.29289 | 541.27691 | 575.33001 | 285.22850 | 268.20195 | 302.25505 |
| 5 | 629.37696 | 611.36639 | 612.35041 | 646.40351 | 356.30200 | 339.27545 | 373.32855 |
| 6 | 700.41407 | 682.40351 | 683.38752 | 717.44062 | 427.33912 | 410.31257 | 444.36566 |
| 7 | 771.48757 | 753.47701 | 754.46102 | 788.51412 | 512.42827 | 495.40172 | 529.45481 |
| 8 | 842.52468 | 824.51412 | 825.49814 | 859.55123 | 626.47119 | 609.44464 | 643.49774 |
| 9 | 913.59818 | 895.58762 | 896.57163 | 930.62473 | 740.55051 | 723.52396 | 757.57705 |
Additional MS/MS fragments
| m/z | Annotation |
|---|---|
| 146.06004 | a’ |
| 174.05495 | a0 |
Recorded MS/MS spectra
| Precursor | Co-eluting | Spider | Source | Author | |
|---|---|---|---|---|---|
References
| Title | Reference | Spider | Name | Content | Link |
|---|---|---|---|---|---|
| Isolation and chemical characterization of a series of new spider toxin (nephilatoxins) in the venom of Joro spider, Nephila clavata | T. Toki, T. Yasuhara, Y. Aramaki, K. Osawa, A. Miwa, N. Kawai, T. Nakajima, Biomed. Res. 1988, 9, 421-428 | N. clavata | Nephilatoxin 4 / NPTX 4 | Amino acid analysis, Activity-studies, wrong structure | Link |
| Polyamine toxins from spiders and wasps | A. Schäfer, H. Benz, W. Fiedler, A. Guggisberg, S. Bienz, M. Hesse, The Alkaloids 1994, 45, 1-125 | N. clavata | NPTX 4 | Review | Link |
| Facile Synthesis of 6-Hydroxyindole-3-acetic acid: on the structure of aromatic subunit of nephilatoxin 1-6 | T. Shinada, M. Miyachi, Y. Itagaki, H. Naoki, K. Yoshihara, T. Nakajima, Tetrahedron Lett. 1996, 37, 7099-7102 | N. clavata | NPTX 4 | partial synthesis, NMR | Link |
| Acylpolyamines: Mass spectrometric analytical methods for Araneidae spider acylpolyamines | Y. Itagaki , T. Nakajima , Toxin Rev. 2000, 19, 23-52 | N. clavata | NPTX 4 | Review | Link |
| A natural combinatorial chemistry strategy in acylpolyamine toxins from Nephilinae orb-web spiders | M. S. Palma, T. Nakajima, Toxin Rev. 2005, 24, 209-234 | N. clavata | NPTX 4 | LC-MS | Link |
Spider species
| Spider species | Family | Discovered |
|---|---|---|
| Nephila clavata | Araneidae | 1996 / T. Shinada |